What is the reader of the Bible to make of Esau, Jacob’s brother? Why is Israel’s neighbor Edom treated so harshly in the prophetic literature? And how might one understand the relationship of these traditions? This study engages these questions by offering a canonical reading of the Esau and Edom traditions of the Hebrew Bible in light of the theological issue of election, looking specifically at the portrayal of Esau and Edom in Genesis, Deuteronomy, and the prophetic material. First, it is argued that the depiction of Esau in Genesis is, on the whole, positive. Though the unchosen son, Esau is blessed and responds well to the challenges life presents him with. Thus, the unchosen brother is by no means cursed or excluded from the divine economy. These motifs find resonance in Deuteronomy, which in particular construes the issue of land possession in explicitly theological language, while reinforcing the kinship motif. Second, it is put forward that Edom is portrayed negatively by the prophets for violating a relationship of brotherhood, and for disrespecting the divine apportioning of the lands. It is this twofold rejection of their brother Israel as well as YHWH who has appointed the lands that helps account for the harsh message of the prophets. And third, it is suggested that these two traditions have resonance with one another based on their overarching theological concerns, heuristically labeled brotherhood and inheritance. Returning to the issue of election, it is proposed that these themes may helpfully be understood within the theological categories of divine initiative and human response, as the response of those involved is taken up in YHWH’s own responsiveness, whether in blessing or judgment.